After last week’s deep dive on outlining, somebody emailed back with a question. They wanted to know what to do when it felt like the book was tugging them off course from the outline that they had set.
They asked: “Is it okay to go back to the outlining phase? Or should you just keep writing and make it work?”
The way a lot of coaches talk about outlining can make it feel like it’s a discrete stage in the writing process—a box to tick off in your project management tool so you can move on to the drafting stage.
Once you have a solid outline, you’re golden.
I find this attitude trips authors up for two reasons.
Cue the performance anxiety!
First, if you go into the outlining phase believing that you have one chance to come up with an amazing outline, it puts a lot of pressure on the process that doesn’t need to be there.
Last week, a book coaching client told me she was nervous about committing her thoughts into an outline because she worried about getting it wrong.
And that’s fair. There are a lot of artistic pursuits where taking a big step feels irreversible.
For example, I love to sew. Right now, I’m working on a red trench coat inspired by the one Emma Stone wears in the movie Bugonia.
I spent hours testing the pattern, ordering sample fabrics, buying the perfect organic cotton twill (hers is wool, but I wanted something lighter), prepping the fabric, and laying out the pattern pieces.
Then I stared at my cutting table a long, long time before I finally grabbed my scissors.
I needed to be absolutely certain of my planning process. If I’d made a mistake, I could end up ruining several yards of this expensive fabric.
The great thing about writing a book is that nothing is ever set in stone.
Until it’s sent to the printers and bound up between covers, everything can be moved and changed and reordered and fixed and improved. From the first few lines of the outline to the polish of the final draft, you can’t screw up your manuscript.
So, go ahead! Write down all your amazing ideas! Play! Get creative! Outlining should be fun, not constricting.
Stuck on the wrong trajectory
The second way writers get tripped up by this thinking is in the drafting process of the book.
In my experience, most books buck the outline at some point.
That’s absolutely okay! You learn more, you refine your argument, and you end up needing to make changes.
If you find yourself doggedly sticking to the outline when your book wants to veer right, you’ll run into trouble.
You might start losing the joy of the writing process. The book might start feeling stale and lackluster. You might start experiencing writer’s block.
Whenever those signals pop up for me, I know that’s my subconscious’ way of telling me that I’ve gone off track somewhere and need to re-evaluate.
Knowing when (and how) to pirouette
Personally, I tend to vacillate between the drafting and outlining process. This is especially true with fiction, but even with nonfiction projects, the act of actually writing the book teaches you so much about what the structure should be.
I’ve sent nearly every one of my ghostwriting clients an email (generally about halfway through the book) saying, “Hey, I took another look at the outline, and I think I’ve figured out a better direction. See attached.”
So what do you do when you have an outline but you feel your book tugging you off course as you’re drafting?
1. Zoom back out to get the big picture
During the initial phase, you used your outline as a planning tool. Now we’re going to use it as a diagnostic tool. Start by grabbing your outline and making sure it matches with what you’ve written already.
Flesh it out with any additional points, details, or changes that you made in your initial chapters.
This can be as detailed or light as you like. The point is to get a clear picture of the book as it already flows.
Then, look at the whole outline and ask yourself:
- Have I learned anything new since I wrote this outline that needs to be included?
- How has my thinking evolved on this topic since I wrote this outline? Is there anything there that needs to be changed?
- Is there any new information that I feel like needs to be added, or anything superfluous that I’ve discovered we don’t need here?
- Is the issue the order of ideas, the clarity of ideas, or something else entirely?
- If I were outlining the book today based on the draft I already have, would I outline the remaining chapters the same way?
2. Walk through your nonfiction book outline with a reader’s POV
Next, imagine you’re reading your book from the perspective of a reader who is unfamiliar with your work. Picture the concepts building on each other. Imagine reading about the different stories, examples, and evidence in that specific order.
What does that imaginary reading experience feel like to you? Does it feel complete? Is there anything missing?
Ask yourself:
- Are there any logical gaps in the framework I’m laying out, the story I’m telling, or the thesis that I am working toward?
- What am I assuming the reader already knows in each chapter? What questions am I answering for them by the end of each chapter?
- Does the reader have all the information here to achieve what I’ve promised them at the beginning of this book?
- Does any information or chapter feel wildly out of place, or does everything go together well?
- Could we make this argument more coherently if we moved things into a different order?
- Does every section here actually serve the reader—not just exit because I like it?
3. Finally, make sure you’re not dealing with a more deeply-seated issue.
Sometimes, especially with projects that are highly personal or complex, you will run into areas of resistance that may not be easily diagnosed from the surface.
If your book still logically makes sense and the outline still seems good, it’s time to look inside.
Ask yourself:
- Has the purpose, theme, or argument of this book shifted as I’ve been writing? In other words, am I secretly trying to write a different book than the one I planned?
- If so, can I reshape this outline to support it? Or should I consider this a separate project?
- Am I resisting the work because things are actually wrong with the outline/structure, or just because writing is hard right now?
- Are there any mindsets or misbeliefs that are creating resistance around my writing (and identity as an author) in this moment?
Know when to move forward
You can cycle between the nonfictino book outline and drafting phase as often as you like, but I will offer a caveat.
When things feel like they’re not working, resist the temptation to throw the entire thing out and start over. The problem is rarely that you need to re-outline the entire book from scratch.
Close the manuscript, take some space, and come back with fresh eyes later.
And if you need an outside perspective to help you make sure you’re writing the book you set out to write, schedule a call. Let’s chat.